


Milkyrolly and the Barnboys - Milking Session

by AnalExtremes



Category: Milkrolly
Genre: Anal Fingering, Anal Fisting, Anal Plug, Anal destruction, Anatomical Descriptions, Bondage, Double Anal Penetration, Extreme Prolapse, Fivesome - M/M/M/M/M, Gangbang, Graphic Description, Hyper cocks, M/M, Milkrolly – Freeform, Prolapse, Rokudenashi, Rokudenashi art, Rosebud – Freeform, Thick and Creamy cum, Very Deep Denetration, Vomiting, anal extremes, anal stretching, bara, bladder penetration, deep penetration, farm, foodplay, graphic anatomical descriptions, huge cocks, prolapse play, puking, urethral Penetration
Language: English
Status: Completed
Published: 2017-10-24
Updated: 2017-10-24
Packaged: 2019-01-10 17:38:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,773
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12304221
Author URL: https://archiveofourown.org/users/AnalExtremes/pseuds/AnalExtremes
Summary: Milkrolly gets a new job in a mysterious farm! Would our hero be ready for it?





	Milkyrolly and the Barnboys - Milking Session

**Author's Note:**

> This is based on a Rokudenashi character and it includes several anal extremes and almost hyper/hyper themes. I tend to love deep penetrations, anal extremes and prolapsed assholes ( also called rosebuds) therefore if you are into these kinks you'll love it! For those who aren't sure about reading this I'd warn them to proceed cautiously. I also created a ([tumblr](https://analextremess.tumblr.com/ask)) to receive prompts because I started writing and I want to get better at it. More info about my preferences in the end notes and my tumblr.

Milkrolly was a 6’4 feet tall man who certainly attracted stares ([link](https://imgur.com/djwCl4l)). He was dressing a very revealing attire, some collared leather harness attached to pink leather straps that intricately run through his body. Those straps adorned his chest and torso accentuating his perfect hunky, manly shape. They were also attached to more straps around his legs, crotch and dick. He was endowed enough to make the largest porn actors feel shy, an incredibly huge shaft barely covered by a small tight black jockstrap pouch. There was another leather strap around his dick, similar to a cock ring. It was connected to the straps on his thighs and crotch. Milky had thigh high socks, they were very tight, some gloves, which had a black spotted cow pattern printed on them. A small fabric cut bearing the same pattern was attached to the leather straps in the middle of his broad chest. A pink toned mask, in the same color of the leather straps, covered most of his face, only his mouth could be clearly seen. Bull horns were attached to the mask. There were three golden small round metal signs, “milk” was written on them. One of the signs was attached to the fabric in the middle of his chest, the other two were on his wrists attached to leather straps adorning his gloves.

Shame wasn't a word on his vocabulary. He comfortably sat down there in the train. People stared at him while he read the newspaper. Disgusted stares, lewd stares, lascivious stares, women and men looked at him but only one thing was on his mind. Milkyrolly was hired for a certain job at a certain farm. He had to travel out of his own hometown but the promise for a high payment and some lewd activities had attracted him. It wasn't that long of a distance to travel but at least two hours away. He dozed off sleeping for a while, news weren't that interesting.

 “Hey, dude. H…Hey…” a scared man touched his shoulder waking him up. “We are on the last stop.” Milky woke up and stood. He thanked the man and walked out of the train. There was a large, eight inches thick and ten inches long plug on his butt. His toy appeared at clear view while he walked. His butt were two perfect globes, round firm but bouncy. It was an amazing view getting the poor train guard rock hard. His butt plug just added insult to injury getting the jaws of that man on the floor. It was pretty much the same thing at the public bathroom. There was a man besides him on the urinal, first he looked on his gigantic penis then before exiting he came around and groped Milky’s big bubble butt. “Well, well… Unfortunately I have something to do and somewhere to go.” Milky said while smirking. He got his dick back into the tiny jockstrap pouch. His length barely concealed because of a half hard boner caused by the butt grabbing. Milky walked away leaving another poor man to his own devices to get where he should go.

A farm carriage was outside the train station waiting for him. “Are you the new guy?” An old man looked at him, wide eyes on a wrinkly face. “Well, I gotta say the boys gon’ love this one and ya are in for a hell of a ride.”

“Well, that’s the reason I accepted the job.” Milky smiled to the older fella walking down to jump on the back of the carriage.

“Well yeah, ma’ boys were looking for someone just like ya for a while now.” The old man looked back eyeing at Milky’s body. He sighed out disappointed. “Heh, wish I’d met someone like ya when I was younger. Anyways mah’ boys gonna have all the fun for themselves.” They traveled for half an hour on a bumpy, unpaved road until arriving at some old wooden gate. “Rodenwell Dairy productions” was written on a big plaque attached to it.

“Yeah, it’s been family business for’a’while now. We have our own goo’ old way to produce our goods!” That old man seemed a bit too excited about his own farm. Perhaps it was some old tradition or something. It took them a few minutes more to get to the barns. There was no one to be seen when they arrived but the old man quickly shouted. “Hey boys, come out. Our new employee has arrived!”

After a few seconds four guys came around, they were behind the big barn. “Here, these are mah’ boys. Derek is the older one, 27 now. Then there’s Jack, 25, Victor 24. Oh and my youngest, Gabe, he’s 18!” Milk looked at his new co-workers having to bite his own lips not to moan in excitement. Derek was a tall 7’8 feet high man, he wore some overalls made out of jeans. Those overalls were unbuttoned and didn’t cover his legs or chest, just some knee long shorts. He had a wide chest and perfect abs along thick thighs and a gargantuan package. His eyes were green accompanied by short wavy light brown hair and tanned skin. Jack had darker skin, black crew cut hair, blue eyes and a bit shorter, 7’5 feet tall. He wore some jeans pants and nothing more. His built was similar to Derek, hunky and muscly. Victor was a bit different. He was pale white, shaved hair, light brown eyes and had a swimmer built. He was similar to Derek and jack when it came to huge packages in between their legs though. The youngest one was smaller, 6’ feet tall wearing overalls and a white shirt. He was slimmer but had some muscle, not a huge package but it wasn’t something to be called small either. Gabe also had short black hair, blue eyes and tan skin similar to Derek.

“What do you think of mah’ boys?” The old man asked.

“Hah, they’re all beautiful!” Milky exclaimed while the crew lasciviously looked at his outfit.

“That must be something from the city, ya know?” Derek looked at his brothers.

“Looks good though, bruh.” Victor smiled.

“Let’s get him inside already!” Gabe shouted.

“Calm down you lil demon. He’s gonna be your first but don’t need to rush things.” Jack smirked coming near his father’s farm carriage to help Milky jumping down. “Whoa, look at wha he’s got there.” Jack swatted Milky’s butt as the brothers ran around to see what he was talking about.

“Ya, we found the right one.” Derek’s eyes went wide seeing Milky’s eight inches thick butt plug. Milky bent his body a bit so everyone could get a good view of his behinds. Then he spread his cushion like, firm ass cheeks. A wildly pulsing sphincter came at view.

“It’s gonna get me hard fur'reals…” Gabe was already rubbing his shaft through his overalls. “Let’s gonna get him inside already…”

“Now I fucking agree. We need to get done for tonight or the cream cheese won’t be ready tomorrow morning.” Victor warned them.

They still spent a minute or so admiring Milky’s body then a few more presentations so Milky could learn who was who and memorize it. There was some explanation about how everything should be done, Milky agreed to their terms right when they opened the barn doors. A few stables were separated by wooden partitions, almost all of them were empty, except the biggest one on the right side.

“We gonna have to stretch you out so our equipment fits.” Derek explained.

There was an iron table with two half round cuts so Milky could position his thighs on them. Jack had gone to get an iron bar. It was a thigh high spreader bar. Victor set it up restraining Milky’s thighs, forcing the big man to keep his legs spread while his thighs perfectly fit the half circle cuts leaving Milky’s buttocks exposed.

“No need for these around here.” Jack cut off the tiny jockstrap. Derek was undressing his overalls letting his hard length out.

“Look Derek, our new toy has a big dick too!” Gabe shouted. Milky’s cock was under the metal table, a huge fifteen inches long, almost five inches thick and diamond hard dick. He was more than excited seeing Derek’s gargantuan dick, nineteen inches long, ten inches thick which made his own cock look a bit small. Jack was the second one followed up by Victor on taking their jeans down. Both Jack and Victor were seventeen inches long but Jack was thicker, eleven inches thick, and Victor was even thicker, twelve inches thick.

“You all getting undressed…” Gabe sighed. “And I have to get the equipment ready!” He had an angry face.

“Nah, wait your turn!” Derek said. “We have plenty of holes to fuck up.” The older brother winked. “But how’s it. Liking the view?” He asked Milky. Those three brothers were standing near each other side by side. Their humongous lengths were throbbing very hard. Derek had his shaft covered in thick veins, more vascular than his brothers. Jack had some veins but Victor’s had almost none.

“Oh I’m loving it!” Milky opened up a wide smile reaching for their lengths as an angry Gabe went away to get something ready. Derek was in the middle, Jack to the left and Victor to the right. Milky groped Jack’s and Victor’s shafts jerking them off. He slapped those meat poles across his face. Thick, slimy precum covered his lips and cheeks in almost no time.

“Open that mouth you slut!” Derek said in an authoritarian tone. Milky opened his mouth as wide as he could but no matter how wide he would open it wouldn’t be enough to fit Derek. Derek hold Milky’s head in place then slowly began inching his dick inside Milky’s warm mouth. It was big enough to slightly dislocate Milky’s jaw. Milky was loudly gagging, he squinted his eyes in pain while his cock steadily discharged thick precum which was collected in a large metallic bowl under the table. Derek’s dick was invading Milky’s throat causing a large bulge to appear on Milky’s neck. Tears were running down his face when that huge length entered his esophagus. His dick throbbed spurting some precum when the large thick piece of meat was deep enough to break his upper stomach sphincter. There was a loud popping noise. His tight stomach sphincter was broken causing him to shake feeling an excruciating amount of pain. His eyes opened widely when his nose hit Derek’s crotch. Milky's stomach was filled by a large dick. Derek’s glans and a bit of his length rubbed against the lower stomach sphincter but not long enough to penetrate and tear it apart. Milky was still furiously jerking of Jack and Victor. Those studs aimed their lengths at his face to cover it up in precum. It was thick, sticky and slimy pre running down to Milky’s chin, drenching his hard nipples and leather strip in the middle of his chest.

Derek tugged away still holding Milky’s head in place. Ten inches of Derek’s length were pulled out, enough to leave Milky’s stomach empty but still be inside his esophagus. The older brother shoved his dick back inside in a violent, rough thrust punishing Milky’s upper stomach sphincter and depositing a large amount of precum inside his guts. That guy repeated this movement three more times then changed his pace to a steadier but still rough and quick movements. Jack and Victor took their own lengths beating each side of Milky’s face with the huge shafts. Milky’s stomach was filled with enough precum to force it through his intestines. Derek fucked his mouth for what was almost ten minutes, punishing his esophagus and breaking his stomach sphincter. That was enough time to fill Milky’s intestines, colon and rectum. His belly was inflated a little bit but not enough to make a big difference.

“Enough of his mouth, now I want to see his cunt.” Derek pushed his cock out of Milky’s mouth causing a loud slurpy and sloppy noise. Milky’s tongue rolled out, thick saliva globs mixed up with slimy precum run down his chin to his chest, tears running down his abused face. It was not a burst but seemed like he was slowly puking precum then he retched letting a good amount of it out. Victor slapped his thick dick across Milky’s face, taking his glans inside Milky’s mouth in a similar way to what Derek was doing. He shoved himself inside Milky’s mouth quickly penetrating the throat, esophagus and stomach. Milky moaned out loud but his moan was muffled by Victor’s dick. Derek had moved behind Milky slapping his bubble butt for a few seconds.

“Damn, he really came prepared just like he said… True anal slut we got here! Open it up bitch!” Despite being roughly mouth fucked by having Victor’s dick raping his broken, fiery upper stomach sphincter he reached behind spreading his buttcheeks as wide as he could. Victor quickly reached out the large butt plug easily removing it. Milky was gaping at least seven inches wide open. Derek got immensely horny looking right into Milky’s rectum. It wasn’t only that, Milky had an eager muscle cunt, eager enough to insert three fingers from each hand inside, spreading it out even more. His guts were filled with precum which had come out of Derek and Victor’s dicks, it got to a point his intestines were also filled with clear dick juices. He started pushing out, literally spurting slimy precum from his asshole. His rectal tissues were shiny red, protruding out to form a prolapse which was at least two inches long. The anal lining hanged out of his swollen asshole pulsing out covered in thick precum and ass juices making it extra shiny.

“Holy fuck!” Jack had moved behind Milky because Derek’s face was completely dazed. Both brothers reached Milky’s wet dangling hole rubbing and playing with it before his insides retracted back to turn just into a wide gape again. “Fuck, Vicky we can even see deep inside his rectum. This whore is so wide that I guess we can even see his colon entrance!” Jack exclaimed shoving his own big fist inside Milky’s overly pliant hole. Derek was a bit too dazed to say anything but he started punching Milky’s asshole exchanging fisting movements with Jack, when one of their punches came out another was shoved inside. Milky was crying, loudly moaning. His own dick was constantly dripping, sometimes even shooting precum on the large bow under him. Victor looked down and spat on Milky's face which was just a big mess at this point, large amounts of thick saliva and precum covering him. Victor was a forceful fucker. He didn’t stop banging his hips against Milky’s face at any point. Milky’s bowels were directly filled by Victor’s excessive precumming to the point his stomach, intestines and colon were filled again resulting in another burst of pre erupting out of Milky’s hole.

Suddenly the fisting motions stopped. Victor clenched his butt while holding Milky’s face in place. He was the first one cumming. Milky’s belly started to inflate when at least five or six litters of cum were shot right inside his stomach. It was enough to travel through Milky’s bowels making its way to his hole. Jack and Derek watched Milky’s asshole prolapsing out, three inches of swollen rectal tissues pushed out, cum erupting of off it as if it was a volcano. Those brothers stared at each other, their hands rubbed and even jerked Milky's protruded out meaty hole. Suddenly Derek pushes Jack aside to start rubbing his immense eleven inches girth dick on Milky’s hole, even a loose anal whore such as Milky looked like a tight virgin near Derek’s beast cock. It didn’t took him long enough to push it in, shoving Milky’s rectum walls back inside again. It was quick and rough, in a second Derek’s shaft was shoved inside straightening up every corner of Milky’s guts. Milky moaned out loud, so loud that even Victor’s dick wasn’t enough to contain his scream of crushing pain and pleasure. He could feel his bowels burning hot, his colon and intestines curves were violently rearranged, forced to adjust to Derek’s size. The pain was even worst around his broken lower stomach sphincter. The had stomach doubled in size from Victor’s cum load, Derek’s precum and the fact that those two huge dick tips were lodged deep inside his belly. 

Victor moaned pushing himself back and out of Milky’s mouth. His glans were sensitive after his orgasm, Derek’s cock was pushing right against him so he had to come out. A loud sloppy noise was emitted from Victor’s move. Milky started retching and vomited precum and cum right after Victor’s shaft was taken out of his mouth. His nostrils were stretched out, thick streams of cock juices and creamy cum loads pouring out of it. Derek positioned his hands on Milky’s shoulders starting to ferociously move his hips, he did small bursting movements at first but roughened his own pace bucking his hips against Milky’s hole at a raging violent rate. Wet noises were coming from that huge asshole and from Milky’s guts. Loud slurps, squelching and even sloshing noises filled the barn. Each one of Derek’s thrust trounced Milky’s entire lower digestive system, abused his lower stomach sphincter and forced the poor anal slut to retch, vomiting more of Victor’s load.

Jack didn’t waste a lot of time, he moved towards Milky’s mouth as soon as Derek was furiously pounding that asshole. Milky had puked and let out a lot of Victor’s load, enough to be able to breath through his nostrils again. He had a grin on his face reaching toward’s Jack’s length having his hands jerking it for a few seconds. “Please break my guts and fill me, wreck my asshole to the point it turns inside out as I'm walking!” Milky exclaimed in his tears, he was taking an enormous amount of abuse and pain but it just got him more and more excited. “And don't forget to pound the hell away of my prostate!” He left Jack’s cock to use his hands to slap his own butt cheeks. Milky opened his mouth as wide as he could while covering his own ass with his hand marks. That lewd exposition had Derek and Jack beyond excited. Derek’s hips were getting as red as Milky’s ass from shoving himself inside at such a violent pace.

On the other side Jack hold Milky by the horns attached to his mask slowly penetrating himself in his open mouth. Milky’s jaws were dislocated a bit to comport Jack’s huge size, more tears ran down his reddened face cheeks. Jack’s method was slow but torturous and abusive, that farmer boy wanted to feel every inch of Milky’s throat and esophagus. He kept going deeper reaching Milky’s upper stomach sphincter to easily slide himself inside his gut, both Derek and Victor’s dicks did a god job at loosening that passage. Milky screamed but it didn’t came out loud, his stomach sphincter was loose but it was sensitive, steaming hot and very sore. He felt Jack’s and Derek’s thick glans fighting for space within his stomach. Both brothers seemed to start a playful competition shoving themselves inside and out of Milky’s stomach. They were getting pretty violent and merciless to the point Derek’s dick was reaching the lower part of Milky’s esophagus and Jack’s dick was reaching the upper parts of Milky’s intestines. They had both their lengths stretching out both of Milky's stomach sphincters.

Milky was enjoying it, enjoying it too much as a matter of fact. Instead of just precum he started pouring out cum. His dick was pulsing, dripping cum at a steady pace similar to an open faucet. His prostate was bruised enough and kept getting hammered producing huge amounts of thick cum loads, quantities that his balls couldn’t hold. There was no other choice but to let it drip out. His hole was pounded, wrecked and broken. Milky’s ass lips were getting swollen, glistening and red. Derek looked down to watch how Milky's asshole started to clench and protrude out. His rectal walls were attached to his shaft in between Milky’s anal rim and his cock every time he tugged away. Milky’s hole was prolapsing, slowly sleeving out to envelope Derek’s dick. The older brother rolled his eyes out of his skull feeling Milky’s guts and anal muscles sucking him as if it was a vacuum tube.

“Fuck, he’s the best anal whore I ever had!” Derek exclaimed still pounding Milky.

“You will have to give us some space soon…” Victor let out a few words sitting down in a hay roll.

“Oh man, you filled all his holes!” Gabe had come back pushing some big tubes and some metallic equipment. “He was supposed to be my first one…” He had a bummed face seeing how his three brothers were already fucking or have fucked Milky.

“He’s gotta a lotta holes, use your imagination…” Victor teased his young brother but Gabe had this disappointed look. “Oh c’mon dude, you don’t have to pretend you're innocent… His dick is a fuckhole too.” The older brother had lost a bit of his patience but Gabe acquired a bit of an excited look.

“Man I had never thought about it!” He exclaimed looking under the table. Gabe undressed his overalls, his dick was big, nineteen inches long but it was much thinner than his brothers. He was a mere six inches thick. Both Derek and Jack had stopped fucking Milky for a few seconds so they could change the iron table height where Milky was lying. They levered to a point where both Derek and Jack could keep fucking Milky but Gabe could go on his knees under the table.

Gabe put the iron bowl filled with cum and precum aside. He was fast to insert two fingers on Milky's urethra. It was a bit tighter than his asshole but Milky had already had his cock fucked plenty of times to quickly open up. Jack and Derek were still hammering their dicks inside Milky's mouth and asshole when Gabe had already slid in a fourth finger inside his urethra. The younger brother couldn't wait too much, he didn't stretch out Milky's urethra enough but just pointed his dick, rubbing it against the gape that was created by his fingers then pushed himself inside. He slowly filled that cock tube until reaching the tighter point at the base. Gabe grinned pushing his hips back then forward to enter Milky's urethra and go inside his bladder. Milky rolled his eyes out of his skull having his asshole, mouth and dick rage fucked. He emitted louder, lusty, pain filled moans. Gabe gripped Milky's dick holding it in place and started fucking it, getting his glans inside and outside of the poor slut's bladder.

Milky was reaching a desperation point. His urethra was fucked up. Gabe was pumping out at least half a cup of precum inside his bladder per thrust while Dereck and Jack ravished his stomach sphincters depositing large amounts of precum in his belly which still had some of Victor’s cum loads. He couldn't even let his own cum loads out of himself because Gabe was blocking his urethra. His belly and bladder were swelling up, Derek and Jack's lengths were visible moving up and down in the torso. His neck and dick were also bulged, the bulge on his dick was growing, accumulating his own cum loads and pre mixed up with Gabe's. Milky’s balls were also swollen. Those cum loads were forced back in there, there was no way he could get them out. There was a need to eject everything out, to piss and cum and to let his bowels free to push out everything. His body reacted trying to retch and puke, trying to piss and cum, trying to push Derek's dick out of his hole but he couldn't, it just ended up in contractions and twitching. His broken bladder, asshole, intestines, stomach and sphincters were trying to eject everything but badly failing at it.

“He's such a goddam slut, look at how he's shaking in pleasure!” Victor exclaimed. "Cum in him already. I need another turn." He requested jerking his rock hard dick.

“Fuck you idiot, now I can't hold anymore!” Derek started cumming, thick large ropes of creamy, condensed milk textured cum. Those burning hot jets hit Jack's dick getting him to immediately start letting his load out. Gabe wasn't experienced. It took him the sounds of his brothers’ moans and Milky's tears to start unloading right inside Milky's bladder. His thick dick head pumped at least seven litters inside it getting Milky's bladder area to bulge under his belly. It wasn't only that area though, Milky's stomach had at least thirty litters of jizz and precum sloshing inside it, not to speak about the amount of thick jizz filling his bloated intestines, rectum and esophagus.

“We have to be very careful now bros, can't waste any jizz. Vick go grab the plugs.” Derek ordered. Victor looked behind at the hay rolls to find three plugs. He walked near his brothers and Milky.

“Watch and learn Gabe. One hole at a time.” Jack gave his younger brother a lesson. The first one was Milky's mouth. Jack slowly removed himself while Milky loudly gagged. Once he was out Milky tried vomiting, Jack quickly plugged his mouth letting some cum escape but forcing Milky to swallow it all, forcing the load to go back inside. Next one was Milky's dick. The same procedure was done, having Gabe slowly push himself out of Milky's cock. They had lost some cum but soon plugged up Milky's dick. The final hole was his asshole. Derek was moving his hips on the way out but he slipped on some jizz in the floor. His dick slid out at an unexpected moment. Milky couldn't hold it inside, his loose, destroyed mancunt bursted out exploding like a cum geyser. The anal whore's hole prolapsed out, six inches of swollen pinkish red rectal meat dangling in between his ass cheeks. The brothers were fast about shoving it back inside and plugging it but they judged that they had lost a lot of jizz in the process.

“Well I guess it's an excuse to punish him for a bad job, he was supposed to keep it all inside.” Vick grinned as he spanked Milky's ass a bit and unlocked the thigh spreader. “Stand in the table.” Milky could barely move. His enormous belly had some jiggle. Sloshing loud noises filled the barn again when the brothers helped him climbing in the iron table. “Spread your legs.” Victor ordered, Milky cried a bit, tears ran down his face as he spread his legs. He had his entire body burning in pain, there was soreness everywhere. His dick still bobbed up and down by itself from how horny he was. Victor slid under Milky. “Remove it Derek and do that…”

Derek removed the plug in a violent push but gave Milky no time to gape or prolapse or anything. He threw the plug near them quickly moving his hands to Milky’s hips lowering him down. Victor was holding his dick in place to impale Milky right away. It was a forceful push, enough pressure on his guts to get Milky’s mouth plug to simply jump out. Milky vomited some cum right away but Derek ran around them climbing in the table to shove his dick deep inside Milky’s throat.

“Fuck him, another bit of jizz lost, this whore deserves some punishment.” Jack talked in a kind off angry, kind of horny tone. He ran around spreading Milky’s butt cheeks trying to push his cock inside while Victor's was already in there. Milky squinted his eyes crying in pain, Jack hold the butt in place inserting his thumbs inside, his hands cupping Milky’s butt. He spread it out stretching Milky’s sphincter mercilessly. When it was wide enough he slid inside and clearly avoided being slow. His hips just banged against Milky's butt until his cock was buried to the hilt inside that broken muscle cunt. Milky was shaking almost passing out. His rectum and intestines were still filled with jizz but now had to accommodate two giant thick cocks inside, both dicks going through his stomach lower sphincter further breaking it apart. Jack pushed himself inside really hard filling Milky’s esophagus and stomach. His dick tip was lodged against his brother’s glans on Milky’s stomach. They bucked and thrust deeper. This time Jack’s dick went through Milky’s lower stomach sphincter while Derek’s and Victor’s penetrated his upper sphincter. All three dicks broke through both stomach sphincters, Victor and Derek’s glans were penetrating the lower part of Milky’s esophagus as Jack’s was entering his upper intestines. Milky’s intestines and those cocks were clearly visible in his belly. There were outlines of his guts moving in his abdomen all the while the jizz and precum loads sloshed through his entire digestive tract, expanding and stretching his internal walls even more. A high amount of pressure was exerted on his body getting Milky to almost beg to eject it all out.

“Ah y’all don’t let me have some fun fuckheads!” Gabe shouted.

“Fuck you lil bitch…” Victor looked at him but had some empathizing moment. “Dang, come here… Sit on my chest and fuck his dick again.” Gabe smiled widely as a kid in a Christmas’ morning. He jumped over to sit on his brother’s chest taking out the plug on Milky’s dick. It was another very fast and deep penetration, his glans filling the swollen bladder, pumping out more precum alongside the jizz. Milky’s dick tube was large at this point, filled with jizz and dick juices. He could only cry and fight his own instincts. His entire body was screaming for release, contractions on his intestines, on his abdomen and an increasing amount of desperation to pee and cum. It was all burning enough to feel like his holes and organs were all in fire. The brothers began to move and fuck him. Violent raging beasts couldn’t reach the pace that they had reached. Loud noises of moans and tears came out of Milky but were all muffled. Milky’s guts, bladder, balls and dick tube were expanding even more, swelling up, filled with cock fluids.

It took the brothers a few more minutes to burst out another couple loads. They pumped a lot of it inside Milky’s every hole. Once done, Milky was filled with at least three to four gallons of jizz on his intestines, belly and esophagus. His bladder had at least ten or twelve litters of cum and a few more of pre filling it. Another few litters were lodged in his dick tube and balls. Every part of his body was swollen and inflated but his belly and bladder were really standing out, especially his large belly, it was double the size of a triplet pregnant belly.

They restarted the processes of plugging Milky’s holes again. Victor handled the mouth plug which was under the table to Jack. Derek took his dick out very quickly but shoved the plug even quicker in the open abused mouth. This time Milky was about to vomit when the plug was shoved inside pushing back everything that was about to come out, heavily dislocating Milky’s jaw to insert it deep enough and reach the throat. Gabe jumped of Victor’s chest giving way into gaped dick. Milky was even losing his senses when his dick was plugged up in the same manner. He was holding onto Victor’s broad chest, looking at Victor’s eyes as if he begged for release.

“Nope, not yet slut. Look at how hard you are!” Victor just smiled back slapping Milky’s sore, stretched out, rock hard dick.

“We have to be fast and coordinated now.” Jack told them. His hands were spreading Milky’s legs apart then he Hold milky by the thighs. “Let your torso lie against mine.” Milky obeyed lying on Jack’s torso. Derek had brought a large butt plug to them so Jack pushed Milky’s body up in the air, away from the table, still holding him against his torso. Derek dashed plugging Milk’s hole as Victor moved from the table where Jack dropped Milky in.

“Good bitch. Now let’s get him ready for the night.” Derek looked at Gabe pointing the metallic equipment and plastic tubes. Gabe was organizing the tubes while Jack and Victor were opening up some compartments hidden in the wooden stable, they had big round openings and some buttons under them. Gabe brought the plastic tubes to his brothers. They had attached and locked them to the round openings. Three tubes were set as Milky watched it all not knowing what was going to happen. There was a small pin attached to each one of the plugs. These pins allowed the brothers to detach a round part of the plugs leaving them hollow. The plastic tubes were attached and locked to each one of the plug’s openings. There was some cum pouring out of Milky’s hole until they quickly turned something on. Air was pumped inside those tubes to keep the jizz and precum inside Milky. Then a viscous yellowish substance dripped inside those tubes. It was very small amounts but they seemed to drip from minute to minute. Air was sucked out and pumped inside the tubes forcing cum to come out and go back inside Milky’s guts, dick and mouth. Victor had prepared some leather straps attaching them to Milky’s legs, thighs, hands and torso. Jack helped him to get Milky’s hands locked on his back and the body locked on the table. Milky’ wouldn’t be able to move, he was already kept in place when Derek brought more straps attaching them to Milky’s shoulder, connecting them on the leg straps. He was completely locked in there.

“He’s good for the night.” Victor said. The brothers got their dirty clothes and simply left the barn. It was something like 9:00 p.m. when they left, after a day of loading their new employee. Milky’s belly was very large at that moment. The loads inside him were slimy, thick and creamy but within an hour or so he realized it was getting thicker. Every time the cum was pushed out of his guts and sloshed back inside it was getting thicker. One hour after the brothers had left Milky was still awake. The pumping had stopped altogether but there was still air pushed up on those tubes to keep the loads inside him, not even a drop dripped from any of Milky’s holes. He was excited and hard but wrecked, tired and fucked up, desperate for any release. Suddenly he started feeling sleepy and sleepier until passing out to sleep for a while. 

* * *

“Wake up…” Victor was touching Milky’s shoulder. “Did we gave him too much sleeping medicine?”

“Nah, I calibrated it just as dad has told me!” Jack replied. Milky was waking up getting a sense of where he was.

“Look he’s waking up, no need to fight.” Gabe’s voice was coming from behind. Milk looked at the clock, it was marking up 9:30 a.m. He seemed to be a bit sedated until Derek came around opening a bottle and forcing him to inhale from it.

“This will do the trick. We need him to be all woke up.” Milky squinted his eyes trying to move his hand, then his body. There were some slow realizations followed up by an explosion of sensations. He had realized he was bound just like last night. His asshole, mouth, and dick plugged up. Then the burning pain on his insides. His stomach, colon, intestines and esophagus were all wrecked. There was a lot of pain coming from any movement he made. Milky finally realized how desperate he was to release everything out but there was no tube attached to the hollowed plugs. He needed to pee, to cum and to release everything but it wasn’t coming out. His guts gargled emitting a loud noise as if he was ready to let out a deep fart, fast deep breaths alongside retching contractions but nothing came out of him. His belly was firmer instead of jiggly. There were no sloshing noises.

Jack and Victor went out while Gabe and Derek took the plugs out and released Milky from the leather straps. The anal slut realized what had happened. He felt something hard but a bit malleable in his throat, asshole and dick. It was something consistent similar to butter but leaning towards frozen butter state. Victor and Jack came back holding a large metallic bowl. This one was large as a mini-pool. Milky could easily lie down in it and that was their plan. Derek had picked up Milky and just moved him to the bowl besides the table. Milky lied on his back, his legs spread apart letting both his dick and asshole very visible.

“Now it’s gonna start to feel better for you.” Derek grinned. They turned something on by plugging something on an electrical outlet. Milky couldn’t quite make what was happening around him.

“You can try expelling it out right now. No one’s gonna fight you, as a matter of fact we need you to do it.” Victor explained. “Try shitting and puking everything out…” He smiled watching Milky starting to move a bit. Milky bore down and pushed out trying to expel what was inside him. His body was also acting out of control. There were contractions on his guts, retching and a big desperation to cum and pee. It all helped him to start letting whatever was inside his body out. There was a large yellowish white log sliding out of his hole, some frozen buttery consistency to it. Milky pushed out more and more. His bruised red asslips were swollen, they pulsed getting pushed outwards. That log went on and on while another thinner but still thick log began to slide out of his gaped urethra hole. All the retching had another log sliding out of his mouth. Milky realized there was a salty but sweet taste. He had deformed grin, then a deformed smile on his face while the log slid out of his mouth. “That’s how they produced the cream cheese in that farm.” He thought to himself.

“It’s gonna get a bit warmer now, to help it melt down.” Gabe warned them. The bowl where Milky lied on was indeed getting warmer. It was nothing but something like warm bathtub water temperature but it was enough to have the cream melting down. That huge log on his hole suddenly broke off after eighteen inches had snaked out of him. It was shaped like his own overstretched guts, knotty and bumpy all over. Milky started retching harder. He could finally vomit since the cream was taking some smoother consistency. His esophagus emptied itself getting him to puke all over his chest and dick. His large urethra gape was spurting everything out as if it had hold urine for days. It showered his belly getting his balls and bladder to slowly empty out.

Milky had some difficult on pushing out some of it though. He was pushing his hole out and forcing himself to try and vomit more but it wouldn’t come out. There was some cream keeping his stomach sphincters clogged. He bore down so hard at a time that his obscenely large gape, which clearly exposed his rectum, prolapsed. It was a bunch of swollen rectal tissues protruding out of his round puffy asshole, at least three inches of it. They were all red, bruised, covered in cream and cum. He pushed out again making it double the size, then again to push his entire rectum inside out. It receded back inside but he pushed it out again and again, trying to unclog his insides but couldn’t.

“Fuck. Too much difficulty. Here take some help.” Jack stood up. He and his brothers were kind of matching today, all of them wearing overalls but in some different ways. His was undone, exposing his muscular chest and huge arms. He then took his shoes and used his right foot to step on Milky’s belly. Milky cried moaning out loud. Loud gurgling, plopping and retching sounds were emitted right after his stomach sphincters were unclogged. Milky pushed out more and more, ejecting everything out. There were some harder pieces, some cum and some softer parts erupting out of his asshole. His hole was flexing and throbbing, pulsing very hard, at times it would protrude out exposing his rectum tissues outside of it. The vomiting was even harder. It dripped through his torso to his swollen, sore balls and cock. 

“Keep it going!” Jack pressed his foot forcefully against Milky’s belly sliding it down to his bladder area. Milky's cock pulsed and throbbed, bobbing around synced to his hole flexing. He was pissing cream mixed with his cum load, thick jets coming out of his gaped out urethra. His hole flexed, winking, opening out to show a rosebud or smaller prolapse and quickly close then relax exposing his gaped anal cave. He didn’t care at all about exposing his rectum walls inside and out, the slut loved it. Milky burst vomited a few times feeling an unbearable pressure inside his guts. “Gotta go clean my feet. Get the hose we have to clean him too.” Jack moved around to clean his own feet while Milky vomited a bit more.

“Get him here.” Gabe got a hose opening it to wash his brother’s feet. Victor and Jack helped Milky to get up and stand. Milky was still vomiting, pissing a bit of cum and pushing cream out of his destroyed asshole. They hold him there for five minutes or so. It was already something like almost two hours of pissing, shitting and puking thick cum mixed with cream. Milky was recuperating his ability to clearly see around him. Those boys had lumpy packages, hard rock dicks inside their overalls. Milky lustily licked his lips smiling.

“Goddamit, I just want to abuse this anal addicted whore again!” Jack exclaimed.

“Not now. We have to follow daddy’s orders.” Victor replied. They kept moving on to where Gabe had the hose. Milky was still puking some, a thinner stream of cum dripping from his wide pisshole. His asshole was gaping, it would prolapse out now and then just from Milky making an effort to take a step forward. Victor grabbed the little clothing ragged fabrics that Milky was dressing ripping them apart and throwing them away. Gabe hosed down Milky’s body cleaning the wet messy fluids. Milky was getting dizzy and overwhelmed. “Was it too much sleep medicine?” Jack’s voice was lower and vanished while Milky slowly fell asleep with the brothers holding him by the arms.

 

* * *

“Oh you woke up again.” They were alone in Victor’s room. There were some very short jeans shorts and a tight t-shirt by the bed. “Push out!” Milky was lying on his belly on Victor’s bed. “Push out already!” Victor slapped Milky’s ass. He felt this wet warm feeling on his now permanently gaped asshole. Victor was rimming him. “Just do it!” Milky obeyed pushing out. His hole pulsed protruding out to form a smaller prolapse. His tissues were still very swollen and sensitive, bruised rectal walls were inside out again. Victor lapped on it while jerking off. Milky let it come back inside as Victor still licked around his big gape.

“You tell anyone about this and I kill you.” Victor stood up. “Dress up and come by the kitchen. I can’t stay here or I’m gonna just rape fuck that hot hole of yours.” He said wiping his chin which was covered by some cream, cum and assjuices. Milky dressed up in the shirt, shorts and went out. There was a hallway leading to the kitchen. His hole was wide open, it wouldn’t close at all. He even easily pushed out a big rosebud. Milky's dick hole was also bigger than ever. His body was pretty sore, stinging inside and out. He entered in the kithen to see the old man who picked him up at the train station. There was also many small glass jars in the table. They were labeled “Rodenwell Dairy productions: Cream Cheese.”

“Oh there ya are. Hope ya had some fun. I was thinking that ya could work for’us anytime. Ya’know your quality’s too good to pass up.” The old man smiled. “I’ll go to the city and sell those. Vick is coming and the boys are spreading tales.” The old man got those jars in a bag and walked out. “Hope I cya’round often.” He winked.

“Oh you there!” Victor sat down besides Milky. His hand traveled down to Milky’s shorts sticking them there. His fingers invading the butt crack, a fist sliding inside Milky very easily. “Hot loose whore! Push out!” He told again rubbing his own dick over the jeans fabric. Victor's hand went out followed by a smaller rosebud protruding out of Milky. Victor rubbed it but had removed his fingers to lick them. “Good, you make the best producer! And again if you tell anyone about this I’ll kill you.”

“C’mon. Come here boys. We have a surprise for you!” Gabe appeared in the corner giving Victor a jump scare. They all walked out to find forty to fifty men outside the farm house. “You know… We thought it would be good to spread around who’s the best anal addicted slut!” Gabe smiled.

“Ready for another round?” Derek shouted from the crowd. Milky turned around as he unzipped his shorts letting them fall to the floor. He squatted down spreading his buttcheeks, three fingers from each hand entering his large hole. Milky forced his hole to open and gape even more. Then he let go of it flexing himself hard enough to have his rectal lining protruding out and coming back inside in a matter of seconds. His dick was already rock hard, bobbing around, dripping precum from his still gaped urethra.

“Thrash all my holes… I just want to be the best fucking anal whore you ever seem!” Cheers came out from the crowd. A bright future was ahead of the hero, Milkyrolly, the best slut around Rodenwell County.

**Author's Note:**

> It was my first work here and I hope you guys like it. I'm also going to write about other guys getting their assholes nailed and extremely wrecked. You can contact me here if you have any request. I may write more chapters about this story if requested. 
> 
> I also created a ([tumblr](https://analextremess.tumblr.com/ask)) to receive prompts since I started writing and want to get better at it. I have a rather big preference for scenes including anal play. When it comes to anal I like everything but here are my favorites: stretching, big insertions, gaping, prolapsing, rosebuds. Other stuff such as oviposition and creative ways of wrecking an asshole are always welcome. Besides that I enjoy pretty much everything! The only big no's are snuff and gore scenes. Blood, scratches and pain is fine but I'm not really turned on by gore. Send me prompts including whatever character(s) you want (no need to be Bara) and the darkest filthiest kinks you have and I'll try to reply them!
> 
> If you got here I'm also taking tips and commissions since my student life got a bit hard! You can contact me through here or my tumblr or this email: hikariluan@gmail.com . Don't worry though, I'll still be posting stuf from time to time when I can. A big thank you to everyone who cared about contacting me with critics and nice words!


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